To answer your questions succinctly,
1. Feller is an outstanding doc...he should be on everyone's top 5.
2. Everybody feels comfortable after different amounts of time. Some people don't like looking bald even if there is no remaining redness and choose to wear hats longer than others. The truth is, nobody knows how long they'll need to wear a hat, since nobody can predict how they'll heal and whether or not shock loss will hit.
3. I wouldn't do postage size procedures. If thats all you need, consider putting off surgery. In a few years, it will be even more refined than it is now (though honestly i'm not sure how ).
4. H&W are top docs, but lots of docs do good hairlines. It boils down to who you feel most comfortable with, in the end.
Sounds like you've already done quite a bit of resarch. Good luck with your decision!